Charlie Youakim is a serial technology entrepreneur with over 15 years of experience growing fintech companies from inception to large-scale success. In 2010, Charlie founded Passport, a leading software and payments service that disrupted the transportation industry with the introduction of white label systems and digital wallets. In 2016, Charlie co-founded Sezzle, where he played a key role in designing the company's technology architecture and driving its growth into one of the leading players in the BNPL space.
From Startup Hustle to Fintech Disruptor
Q. You started your career writing code before launching Passport and later Sezzle. Looking back, was there a single moment when you knew fintech was going to be your life's work?
A. I'd say the moment came back at Passport. I was standing in a parking lot, stuffing cash into an envelope to pay, and thought, "This is crazy. There has to be a better way." Writing code to solve that problem showed me how powerful fintech could be in fixing everyday frustrations. Later, with Sezzle, when I saw young consumers finally get fair access to credit, that's when I knew... this is what I want to spend my next chapter building.
Q. Entrepreneurs often talk about "fail fast" lessons. What was the hardest setback that ended up becoming a turning point in your journey?
A. The biggest setback was actually Sezzle's first model. We launched in 2017 with a debit-based product, and it completely flopped. It was humbling. But that failure forced us to really listen to our customers and rethink the problem—access to credit for young people. That pivot led us to the BNPL model, and it changed everything. Without that failure, Sezzle wouldn't exist as it does today.
Q. Sezzle's roots are in Minneapolis, far from Silicon Valley. How has being outside the usual tech bubble influenced the way you've built the company?
A. Being in Minneapolis has actually been an advantage. We've had to build the company with grit and practicality instead of chasing trends. It kept us focused on solving real problems, not just building what's popular in Silicon Valley. That Midwest mindset of resilience and common sense has shaped Sezzle from the start—and it's worth noting that some of the best tech minds are coming out of Minneapolis right now. You don't need to sit in Silicon Valley to attract Silicon Valley–level talent.
Tech for Good: Building Credit & Expanding Access
Q. Sezzle has branded itself not just as a "buy now, pay later" player but as a tool for financial empowerment. How are you using technology to help underserved communities build credit responsibly?
A. Our mission has always been bigger than just "buy now, pay later." A huge part of it is giving underserved consumers access to credit, but in a way that's transparent and responsible. With tools like Sezzle Up, shoppers can build their credit history by making on-time payments, and we report that to the credit bureaus. We're also layering in financial education, so people don't just get credit—they learn how to use it wisely. For me, that's where fintech makes the biggest impact: not just helping people buy something today, but helping them build a stronger future.
Q. Beyond payments, how do you see Sezzle playing a role in financial literacy and education for the next generation?
A. I grew up in a family of 6 children with immigrant parents who worked tirelessly to build a life for their family. That experience shaped how I see Sezzle's mission. For us, it's never been just about payments; it's about opportunity. Too many young people and underserved communities are shut out of the financial system, and that holds them back.
With Sezzle, we want to change that. Tools like Sezzle Up give consumers the chance to build credit with everyday purchases, while our Money IQ feature makes learning about money engaging and approachable. Our vision is that every interaction with Sezzle helps people not just buy something today, but move closer to financial independence tomorrow.
Competing in a Crowded Field
Q. The BNPL space is crowded, with giants like Klarna, Affirm, and Afterpay. As the self-proclaimed underdog, what's your edge?
A. We've always embraced being the underdog. The big players have scale, but our edge is focus; we're relentlessly consumer-first. That means higher approval rates, tools, and product features our shoppers are asking for, and a mission rooted in financial empowerment, not just transactions. We've proven that you don't have to be the biggest to win—you just have to create real value for both shoppers and merchants. That's what sets us apart.
Looking Ahead
Q. BNPL is still a small fraction of the U.S. payments market. Where do you see it heading, and how does Sezzle expand responsibly without losing its identity?
A. BNPL is still just scratching the surface in the U.S., and I think it's going to become a mainstream way people manage everyday purchases. The key for us is scaling in a way that stays true to our roots—being transparent, fair, and consumer-first. Growth isn't just about volume; it's about making sure the products we build actually help people use credit responsibly. That's how we expand without losing who we are.
Q. Finally, if you could give one piece of advice to the next wave of fintech founders, especially those who want to build mission-driven companies, what would it be?
A. My advice would be simple: don't be afraid to fail. Every entrepreneur will fail—products flop, funding falls through, ideas miss the mark. That's fine, because failure is how you learn. But as I always tell my team: "Failing is fine. But failure is not an option." As long as you keep moving, listening, and iterating, those setbacks become the foundation for your success.
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